Dynamic processes in organolithium chemistry: Tetrameric and 'open' tetrameric chiral α-amino lithium alkoxides

New Journal of Chemistry

Volumn 23, Issue 1, 1999, Pages 35-41

  Armstrong, David R ^a   Davies, John E ^b   Davies, Robert P ^b   Raithby, Paul R ^b   Snaith, Ronald ^b   Wheatley, Andrew E H ^b  

^a UNIVERSITY OF STRATHCLYDE   (United Kingdom)

^b UNIVERSITY OF CAMBRIDGE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

BENZALDEHYDE; LITHIUM DERIVATIVE; ORGANOLITHIUM COMPOUND; TETRAMER;

ARTICLE; CHEMICAL STRUCTURE; CHIRALITY; MOLECULAR DYNAMICS; ORGANIC CHEMISTRY; PRIORITY JOURNAL; SYNTHESIS;

EID: 0032790259     PISSN: 11440546     EISSN: None     Source Type: Journal    
DOI: 10.1039/a808050j     Document Type: Article

References (45)

1. For reviews, see: P. J. Cox and N. S. Simkins, Tetrahedron: Asymmetry, 1991, 2, 1; K. Koga, Pure Appl. Chem., 1994, 66, 1487; N. S. Simpkins, Pure Appl. Chem., 1996, 68, 691; N. S. Simpkins, in Advanced Asymmetric Synthesis., ed. G. R. Stephenson, Chapman & Hall, London, 1996, pp. 111-125; P. Beak, A. Basu, D. J. Gallagher, Y. S. Park and S. Thayumanavan, Acc. Chem. Res., 1996, 29, 552.
2. For reviews, see: P. J. Cox and N. S. Simkins, Tetrahedron: Asymmetry, 1991, 2, 1; K. Koga, Pure Appl. Chem., 1994, 66, 1487; N. S. Simpkins, Pure Appl. Chem., 1996, 68, 691; N. S. Simpkins, in Advanced Asymmetric Synthesis., ed. G. R. Stephenson, Chapman & Hall, London, 1996, pp. 111-125; P. Beak, A. Basu, D. J. Gallagher, Y. S. Park and S. Thayumanavan, Acc. Chem. Res., 1996, 29, 552.
3. For reviews, see: P. J. Cox and N. S. Simkins, Tetrahedron: Asymmetry, 1991, 2, 1; K. Koga, Pure Appl. Chem., 1994, 66, 1487; N. S. Simpkins, Pure Appl. Chem., 1996, 68, 691; N. S. Simpkins, in Advanced Asymmetric Synthesis., ed. G. R. Stephenson, Chapman & Hall, London, 1996, pp. 111-125; P. Beak, A. Basu, D. J. Gallagher, Y. S. Park and S. Thayumanavan, Acc. Chem. Res., 1996, 29, 552.
4. For reviews, see: P. J. Cox and N. S. Simkins, Tetrahedron: Asymmetry, 1991, 2, 1; K. Koga, Pure Appl. Chem., 1994, 66, 1487; N. S. Simpkins, Pure Appl. Chem., 1996, 68, 691; N. S. Simpkins, in Advanced Asymmetric Synthesis., ed. G. R. Stephenson, Chapman & Hall, London, 1996, pp. 111-125; P. Beak, A. Basu, D. J. Gallagher, Y. S. Park and S. Thayumanavan, Acc. Chem. Res., 1996, 29, 552.
5. For reviews, see: P. J. Cox and N. S. Simkins, Tetrahedron: Asymmetry, 1991, 2, 1; K. Koga, Pure Appl. Chem., 1994, 66, 1487; N. S. Simpkins, Pure Appl. Chem., 1996, 68, 691; N. S. Simpkins, in Advanced Asymmetric Synthesis., ed. G. R. Stephenson, Chapman & Hall, London, 1996, pp. 111-125; P. Beak, A. Basu, D. J. Gallagher, Y. S. Park and S. Thayumanavan, Acc. Chem. Res., 1996, 29, 552.
6. H. W. Gschwend and H. R. Rodriguez, Org. React., 1979, 26, 1; I. Omae, Chem. Rev., 1979, 79, 287; P. Beak and V. Snieckus, Acc. Chem. Res., 1982, 15, 306; N. S. Narasimhan and R. S. Mali, Synthesis, 1983, 957; N. S. Narasimhan and R. S. Mali, Top. Curr. Chem., 1987, 138, 63; V. Snieckus, Chem. Rev., 1990, 90, 879.
7. H. W. Gschwend and H. R. Rodriguez, Org. React., 1979, 26, 1; I. Omae, Chem. Rev., 1979, 79, 287; P. Beak and V. Snieckus, Acc. Chem. Res., 1982, 15, 306; N. S. Narasimhan and R. S. Mali, Synthesis, 1983, 957; N. S. Narasimhan and R. S. Mali, Top. Curr. Chem., 1987, 138, 63; V. Snieckus, Chem. Rev., 1990, 90, 879.
8. H. W. Gschwend and H. R. Rodriguez, Org. React., 1979, 26, 1; I. Omae, Chem. Rev., 1979, 79, 287; P. Beak and V. Snieckus, Acc. Chem. Res., 1982, 15, 306; N. S. Narasimhan and R. S. Mali, Synthesis, 1983, 957; N. S. Narasimhan and R. S. Mali, Top. Curr. Chem., 1987, 138, 63; V. Snieckus, Chem. Rev., 1990, 90, 879.
9. H. W. Gschwend and H. R. Rodriguez, Org. React., 1979, 26, 1; I. Omae, Chem. Rev., 1979, 79, 287; P. Beak and V. Snieckus, Acc. Chem. Res., 1982, 15, 306; N. S. Narasimhan and R. S. Mali, Synthesis, 1983, 957; N. S. Narasimhan and R. S. Mali, Top. Curr. Chem., 1987, 138, 63; V. Snieckus, Chem. Rev., 1990, 90, 879.
10. H. W. Gschwend and H. R. Rodriguez, Org. React., 1979, 26, 1; I. Omae, Chem. Rev., 1979, 79, 287; P. Beak and V. Snieckus, Acc. Chem. Res., 1982, 15, 306; N. S. Narasimhan and R. S. Mali, Synthesis, 1983, 957; N. S. Narasimhan and R. S. Mali, Top. Curr. Chem., 1987, 138, 63; V. Snieckus, Chem. Rev., 1990, 90, 879.
11. H. W. Gschwend and H. R. Rodriguez, Org. React., 1979, 26, 1; I. Omae, Chem. Rev., 1979, 79, 287; P. Beak and V. Snieckus, Acc. Chem. Res., 1982, 15, 306; N. S. Narasimhan and R. S. Mali, Synthesis, 1983, 957; N. S. Narasimhan and R. S. Mali, Top. Curr. Chem., 1987, 138, 63; V. Snieckus, Chem. Rev., 1990, 90, 879.
12. D. L. Comins and J. D. Brown, J. Org. Chem., 1984, 49, 1078.
13. D. L. Comins and M. O. Killpack, J. Org. Chem., 1987, 52, 104.
14. D. L. Comins and J. D. Brown, Tetrahedron Lett., 1981, 22, 4213; D. L. Comins, J. D. Brown and N. B. Mantlo, ibid., 1982, 23, 3979; D. L. Comins and J. D. Brown, J. Org. Chem., 1989, 54, 3730.
15. D. L. Comins and J. D. Brown, Tetrahedron Lett., 1981, 22, 4213; D. L. Comins, J. D. Brown and N. B. Mantlo, ibid., 1982, 23, 3979; D. L. Comins and J. D. Brown, J. Org. Chem., 1989, 54, 3730.
16. D. L. Comins and J. D. Brown, Tetrahedron Lett., 1981, 22, 4213; D. L. Comins, J. D. Brown and N. B. Mantlo, ibid., 1982, 23, 3979; D. L. Comins and J. D. Brown, J. Org. Chem., 1989, 54, 3730.
17. E. M. Arnett, M. A. Nichols and A. T. McPhail, J. Am. Chem. Soc., 1990, 112, 7059; M. A. Nichols, A. T. McPhail and E. M. Arnett, ibid., 1991, 113, 6222.
18. E. M. Arnett, M. A. Nichols and A. T. McPhail, J. Am. Chem. Soc., 1990, 112, 7059; M. A. Nichols, A. T. McPhail and E. M. Arnett, ibid., 1991, 113, 6222.
19. (a) G. Hilmersson and Ö. Davidsson, J. Organomet. Chem., 1995, 489, 175.
20. (b) G. Hilmersson and Ö. Davidsson, Organometallics, 1995, 14, 912.
21. (c) G. Hilmersson and Ö. Davidsson, J. Org. Chem., 1995, 60, 7660.
22. (d) H. J. Reich and K. J. Kulicke, J. Am. Chem. Soc., 1995, 117, 6621.
23. (e) J. M. Saá, G. Martorelli and A. Frontera, J. Org. Chem., 1996, 61, 5194.
24. (f) K. Sugasawa, M. Shindo, H. Noguchi and K. Koga, Tetrahedron Lett., 1996, 37, 7377.
25. A. Tatsukawa, K. Kawatake, S. Kanemasa and J. M. Rudzinski, J. Chem. Soc., Perkin Trans. 2, 1994, 2525; R. K. Dress, T. Rölle and R. W. Hoffmann, Chem. Ber., 1995, 128, 673; L. M. Pratt and I. M. Khan, Tetrahedron Lett., 1995, 6, 2165; G. Fraenkel, S. Subramanian and A. Chow, J. Am. Chem. Soc., 1995, 117, 6300.
26. A. Tatsukawa, K. Kawatake, S. Kanemasa and J. M. Rudzinski, J. Chem. Soc., Perkin Trans. 2, 1994, 2525; R. K. Dress, T. Rölle and R. W. Hoffmann, Chem. Ber., 1995, 128, 673; L. M. Pratt and I. M. Khan, Tetrahedron Lett., 1995, 6, 2165; G. Fraenkel, S. Subramanian and A. Chow, J. Am. Chem. Soc., 1995, 117, 6300.
27. A. Tatsukawa, K. Kawatake, S. Kanemasa and J. M. Rudzinski, J. Chem. Soc., Perkin Trans. 2, 1994, 2525; R. K. Dress, T. Rölle and R. W. Hoffmann, Chem. Ber., 1995, 128, 673; L. M. Pratt and I. M. Khan, Tetrahedron Lett., 1995, 6, 2165; G. Fraenkel, S. Subramanian and A. Chow, J. Am. Chem. Soc., 1995, 117, 6300.
28. A. Tatsukawa, K. Kawatake, S. Kanemasa and J. M. Rudzinski, J. Chem. Soc., Perkin Trans. 2, 1994, 2525; R. K. Dress, T. Rölle and R. W. Hoffmann, Chem. Ber., 1995, 128, 673; L. M. Pratt and I. M. Khan, Tetrahedron Lett., 1995, 6, 2165; G. Fraenkel, S. Subramanian and A. Chow, J. Am. Chem. Soc., 1995, 117, 6300.
29. O. Graalmann, U. Klingebiel, W. Clegg, M. Hasse and G. M. Sheldrick, Angew. Chem., 1984, 96, 904; Angew. Chem., Int. Ed. Engl., 1984, 23, 891; J. T. B. H. Jastrzebski, G. van Koten, M. J. N. Christophersen and C. H. Stam, J. Organomet. Chem., 1985, 292, 319; G. W. Klumpp, Recl. Trav. Chim. Pays-Bas., 1986, 105, 1; T. Maetzke and D. Seebach, Organometallics, 1990, 9, 3032; S. C. Ball. I. Cragg-Hine, M. G. Davidson, R. P. Davies, M. I. Lopez-Solera, P. R. Raithby, D. Reed, R. Snaith and E. M. Vogl, J. Chem. Soc., Chem. Commun., 1995, 2147.
30. O. Graalmann, U. Klingebiel, W. Clegg, M. Hasse and G. M. Sheldrick, Angew. Chem., 1984, 96, 904; Angew. Chem., Int. Ed. Engl., 1984, 23, 891; J. T. B. H. Jastrzebski, G. van Koten, M. J. N. Christophersen and C. H. Stam, J. Organomet. Chem., 1985, 292, 319; G. W. Klumpp, Recl. Trav. Chim. Pays-Bas., 1986, 105, 1; T. Maetzke and D. Seebach, Organometallics, 1990, 9, 3032; S. C. Ball. I. Cragg-Hine, M. G. Davidson, R. P. Davies, M. I. Lopez-Solera, P. R. Raithby, D. Reed, R. Snaith and E. M. Vogl, J. Chem. Soc., Chem. Commun., 1995, 2147.
31. O. Graalmann, U. Klingebiel, W. Clegg, M. Hasse and G. M. Sheldrick, Angew. Chem., 1984, 96, 904; Angew. Chem., Int. Ed. Engl., 1984, 23, 891; J. T. B. H. Jastrzebski, G. van Koten, M. J. N. Christophersen and C. H. Stam, J. Organomet. Chem., 1985, 292, 319; G. W. Klumpp, Recl. Trav. Chim. Pays-Bas., 1986, 105, 1; T. Maetzke and D. Seebach, Organometallics, 1990, 9, 3032; S. C. Ball. I. Cragg-Hine, M. G. Davidson, R. P. Davies, M. I. Lopez-Solera, P. R. Raithby, D. Reed, R. Snaith and E. M. Vogl, J. Chem. Soc., Chem. Commun., 1995, 2147.
32. O. Graalmann, U. Klingebiel, W. Clegg, M. Hasse and G. M. Sheldrick, Angew. Chem., 1984, 96, 904; Angew. Chem., Int. Ed. Engl., 1984, 23, 891; J. T. B. H. Jastrzebski, G. van Koten, M. J. N. Christophersen and C. H. Stam, J. Organomet. Chem., 1985, 292, 319; G. W. Klumpp, Recl. Trav. Chim. Pays-Bas., 1986, 105, 1; T. Maetzke and D. Seebach, Organometallics, 1990, 9, 3032; S. C. Ball. I. Cragg-Hine, M. G. Davidson, R. P. Davies, M. I. Lopez-Solera, P. R. Raithby, D. Reed, R. Snaith and E. M. Vogl, J. Chem. Soc., Chem. Commun., 1995, 2147.
33. O. Graalmann, U. Klingebiel, W. Clegg, M. Hasse and G. M. Sheldrick, Angew. Chem., 1984, 96, 904; Angew. Chem., Int. Ed. Engl., 1984, 23, 891; J. T. B. H. Jastrzebski, G. van Koten, M. J. N. Christophersen and C. H. Stam, J. Organomet. Chem., 1985, 292, 319; G. W. Klumpp, Recl. Trav. Chim. Pays-Bas., 1986, 105, 1; T. Maetzke and D. Seebach, Organometallics, 1990, 9, 3032; S. C. Ball. I. Cragg-Hine, M. G. Davidson, R. P. Davies, M. I. Lopez-Solera, P. R. Raithby, D. Reed, R. Snaith and E. M. Vogl, J. Chem. Soc., Chem. Commun., 1995, 2147.
34. O. Graalmann, U. Klingebiel, W. Clegg, M. Hasse and G. M. Sheldrick, Angew. Chem., 1984, 96, 904; Angew. Chem., Int. Ed. Engl., 1984, 23, 891; J. T. B. H. Jastrzebski, G. van Koten, M. J. N. Christophersen and C. H. Stam, J. Organomet. Chem., 1985, 292, 319; G. W. Klumpp, Recl. Trav. Chim. Pays-Bas., 1986, 105, 1; T. Maetzke and D. Seebach, Organometallics, 1990, 9, 3032; S. C. Ball. I. Cragg-Hine, M. G. Davidson, R. P. Davies, M. I. Lopez-Solera, P. R. Raithby, D. Reed, R. Snaith and E. M. Vogl, J. Chem. Soc., Chem. Commun., 1995, 2147.
35. J. E. Davies, P. R. Raithby, R. Snaith and A. E. H. Wheatley, Chem. Commun., 1997, 1721.
36. M. Pink, G. Zahn and J. Sieler, Z. Allorg. Allg. Chem., 1994, 620, 749.
37. G. Boche, K. Harms, M. Marsch and F. Schubert, Chem. Ber., 1994, 127, 2193.
38. A. J. Edwards, M. A. Paver, P. R. Raithby, C. A. Russell and D. S. Wright, J. Chem. Soc., Dalton Trans., 1993, 3265.
39. C. L. Raston, B. W. Skelton, C. R. Whitaker and A. H. White, Aust. J. Chem., 1988, 41, 1925.
40. K. Scott, J. Keeler, Q. N. Van and A. J. Shaka, J. Magn. Reson., 1997, 125, 302.
41. The ability of δ-N-Li interactions in α-amino lithium alkoxides of this type to rapidly cleave and reform in non-donor solution has been observed by NMR spectroscopy: W. Clegg, S. T. Liddle, R. Snaith and A. E. H. Wheatley, New J. Chem., 1998, 1323.
42. M. G. Davidson, R. Snaith, D. Stalke and D. S. Wright, J. Org. Chem., 1993, 58, 2810.
43. G. M. Sheldrick, Acta Crystallogr., Sect. A, 1990, 46, 467; SHELXTL-PLUS, Program for Structure Solution and Refinement, University of Göttingen, 1991.
44. G. M. Sheldrick, Acta Crystallogr., Sect. A, 1990, 46, 467; SHELXTL-PLUS, Program for Structure Solution and Refinement, University of Göttingen, 1991.
45. G. M. Sheldrick, SHELXL-93, Program for Crystal Structure Refinement, University of Göttingen, 1993.